反応 #52847
ord-4ce7c23667ed4c469af66e055671ecc8
反応方程式
反応物
反応条件
後処理
- 1workup.STIRRINGThe resulting solution was stirred at −78° C. to room temperature for 1 h
- 2workup.STIRRINGThe resulting mixture was stirred at room temperature for 10 min
- 3温度heated at 50° C. for 1 h
- 4その他The reaction was quenched by the addition of sat. aqueous NH4Cl
- 5抽出The mixture was extracted with EtOAc (2×)
- 6洗浄washed with brine
- 7乾燥The organic phase was dried over Na2SO4
- 8濃縮concentrated in vacuo
- 9その他The crude material product was purified by flash chromatography (silica, 15% ethyl acetate in hexanes)
実験手順
A solution of lithiothiophene was prepared by the addition of 0.10 g (0.095 mL, 1.2 mmol) of thiophene to a cold solution (−78° C.) of 0.61 g (0.90 mL, 1.4 mmol, 1.6 M in hexanes) of n-butyl lithium in 2.0 mL of tetrahydrofuran. The solution was stirred at −78° C. for 35 min and then a solution of 0.158 g (1.2 mmol) of zinc chloride in 2.0 mL of tetrahydrofuran was added. The resulting solution was stirred at −78° C. to room temperature for 1 h and then the organozinc was added via cannula to a mixture of 0.212 g (0.44 mmol) of ethyl (E)-4-[2-(5,5-dimethyl-8-(trifluoromethylsulfonyl)oxy-5,6-dihydronaphthalen-2-l)ethenyl] benzoate (Compound A9) and 18 mg (0.016 mmol) of tetrakis(triphenylphosphine)palladium(0) in 2.0 mL of tetrahydrofuran. The resulting mixture was stirred at room temperature for 10 min and then heated at 50° C. for 1 h. The reaction was quenched by the addition of sat. aqueous NH4Cl. The mixture was extracted with EtOAc (2×), and washed with brine. The organic phase was dried over Na2SO4 and then concentrated in vacuo. The crude material product was purified by flash chromatography (silica, 15% ethyl acetate in hexanes) to afford the title compound as a solid.